


Playtime

by NavajoLovesDestiel



Category: Supernatural
Genre: Alternate Universe, Anal Sex, BDSM, Dom Castiel, M/M, Medical Kink, Orgasm Delay/Denial, Porn, Smut, Speculum, Sub Dean
Language: English
Status: Completed
Published: 2018-06-24
Updated: 2018-06-26
Packaged: 2019-05-27 20:47:36
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 2,931
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15032963
Author URL: https://archiveofourown.org/users/NavajoLovesDestiel/pseuds/NavajoLovesDestiel
Summary: Dean wants to try role play





	1. Chapter 1

**Author's Note:**

  * For [Shannon-Kind (Shannon_Kind)](https://archiveofourown.org/users/Shannon_Kind/gifts).



> I wrote this for my friend Shannon_Kind. It's pure porn.

Dean whined. “Please, please, Sir?” He tried to make puppy eyes, but he knew he wasn’t nearly as good at it as Sam was.

Cas rolled his eyes. “I just don’t seem the point, Dean. We would both know it was just us. And I’m not that good at pretending.”

Dean sighed. “It would just be for fun. I mean, can’t we just try? Please… just for me?”

Cas closed his eyes. Dean had been begging to try some roleplay for months now. While he didn’t see how it could be fun, Dean was still such a good boy for him.

“Fine. We’ll give it a try.”

Dean hugged his with a huge grin on his face. “Thank you! Sir, I swear if you don’t enjoy it, I’ll never ask again.”

Cas huffed. “Yeah,, we’ll see about that. So, what do you want to try?”

 

They decided to start with something easy. 

 

Dean sat at a table in the bar, drinking on a beer and looking around.

When the guy walked up to him, he looked up into blue eyes.

“Is this seat taken?” 

Fuck, that voice! It sounded like someone had drug silk over gravel.

“N-no, it isn’t. “

The guy sat down. “Can I buy you a drink?”

Dean let out a breath. “Yeah, that would be nice.”

He looked the stranger up and down. The guy had dark hair that looked like someone had been tugging on it. His eyes were a startling shade of blue and the stubble on his sharp jaw made Dean wonder what it would feel like on his inner thigh.

The waitress brought two beers and the guy took a long swallow. Dean watched the way the guy’s lips looked around the rim, and how his adam’s apple looked as he swallowed. He felt a twinge in his groin.

The man smiled at him. “You’re very beautiful.” He put his hand on Dean’s thigh and gave it a squeeze.

Dean gulped. “T-thank you. You’re not too bad yourself.”

The guy lifted one eyebrow and gave him a look that went straight to Dean’s cock.

Of course, it didn’t hurt that the guy was running his hand up Dean’s thigh and to the crease of his groin. It paused there, and Dean had to suppress a moan.

Then the hand rubbed over his cock and he did moan. He went hard and tried not to push his hips into the guy’s hand. But of course, he did. He couldn’t help it.

The guy’s eyes got dark. “I’m going to the bathroom. You follow me in a minute. Understand?”

Dean nodded, afraid to speak. He watched the guy get up and head to the bathroom, and struggled to not just jump up.

When he was pretty sure a minute had passed, he got up and strolled casually to the bathroom. 

When he got inside, the guy grabbed him by his shirt, reaching behind him to lock the door. He pulled Dean into the handicapped stall.

His eyes were dark. “On your knees. Blow me, boy.”

Dean gulped and dropped to his knees, briefly thinking about how dirty the floor probably was. But he looked up into the guy’s eyes and all thought left his brain. 

He reached up and undid the guys’ pants, pulling the zipper down slowly. He reached into the pants and discovered the guy was going commando. That just made it hotter to Dean. He pulled out the guy’s dick and it was hard as stone.

A glistening drop of precum pearled at the tip. Dean swiped his tongue over it, tasting the tang. His mouth was watering.

He sucked the tip into his mouth, and the guy put a hand on his head. Dean loved the taste of it, the feeling on his tongue. He sucked down about half way and thrilled to the hiss the guy made.

He pulled back up, until just the head was in his mouth. He swirled his tongue under it and then sucked down, farther this time.

He used a hand to reach into the guy’s pants and fondle his balls as he sucked up and down, going lower every time. Soon, he had the head at the back of his throat.

The man grabbed a handful of his hair, and pulled. Dean moaned around the cock.

The guy pulled Dean’s head back by his hair, and Dean looked up. The man looked like he was enjoying what Dean was doing. But he held Dean’s head still.

Then the guy shoved his cock into Dean’s throat. Dean gagged but kept his cool. He couldn’t breathe but he was still sure the guy wasn’t out to kill him, so he waited.

Just as his sight began to get dark, the guy pulled back and Dean took a gasping breath. 

The man fucked his face hard, hitting his throat every time. But he always pulled back so Dean could breathe. Dean’s cock was aching in his jeans. He wanted to open his pants and grab it, but he knew it would be a mistake. 

Finally, the guy moaned and thrust in harder than ever. He held there. 

Dean knew what was coming, and he was prepared for it. When the guy came, Dean swallowed repeatedly, managing to get it all. He sucked for the last few drops and then the man pulled Dean's head off by his hair.

Dean looked up at him again. His face was flushed, and Dean felt proud that he caused that.

The guy just tucked himself back in his pants, zipped up, turned and left. Dean pulled himself up with a groan at the way his knees protested.

He pulled his cock out and it only took a few pulls before he was coming in the toilet.

 

“Did you enjoy yourself, Sir?”

Cas smiled. “I did. It was very… different. I can see the appeal.”

Dean smiled and curled even closer. “So, that means we can do it again, Sir?”

Cas nodded. “I am already thinking of possible scenarios. Would you like that, boy?”

Dean nodded sleepily. “I’d love that…” he said as he drifted off to sleep.

 


	2. Chapter 2

Dean walked into the play room. He stopped to look at the exam table that stood there. He wondered where Cas had gotten it, but then again, Cas was resourceful that way. If he wanted something, he got it some way or another.

Cas had told him to lay down on it naked, and Dean did just that. He was cold, but he wasn’t sure if it was the room temperature or his anticipation. He waited.

After a few minutes, Cas walked in. He had on a doctor’s lab coat, with a stethoscope around his neck. He had on his horn-rimmed glasses that Dean thought made him look sexier than hell. For all the world, he looked like a real doctor.

Cas glanced at the folder in his hand.

“So, Mr… Winchester. I’m Dr. Milton. I’ll be doing your exam today.”

Dean nodded. “Okay. Nice to meet you, Dr. Milton.”

The doctor just hummed and sat the file on a table nearby. He walked to where Dean was laying and looked stern . Dean felt incredibly vulnerable being naked on the exam table but it kind of thrilled him too.

Dr. Milton put a hand on either side of Dean’s head and ran his thumbs over Dean’s forehead. It was all Dean could do not to lean into those hands. 

The doctor then ran his fingers down under Dean’s jaw, and down his throat. Dean idly wondered where Cas had learned to do such a good imitation of a doctor.

When the doctor ran his hands over Dean’s shoulders, Dean bit back a moan. Then the hands were on his pecs, fingers probing. When they got to Dean’s nipples, the doctor pinched them and Dean gasped. 

Unfazed, The doctor continued to move his hands over Dean’s chest and down over his abdomen. Dean’s cock was getting hard. Dr. Milton looked at it and smiled.

“Patient is capable of an erection” he noted. Dean blushed.

When the doctor put his hand on Dean’s cock, Dean did moan. The doctor squeezed Dean’s cock and then let go, much to Dean’s unhappiness. 

“Fully erect. That’s good.”

But then the good doctor lifted Dean’s balls and rolled them around in his palm. Dean resisted the urge to wiggle, but only by a little. The doctor seemed to be feeling them all over, and Dean was diamond hard.

When those hands slid under Dean’s balls and rubbed his perineum, Dean groaned. 

When the doctor stood back, Dean looked at him, wondering what was next.  Cas (no wait,  _ Dr. Milton _ ) snapped on a rubber glove. He grabbed a tube of KY jelly and ran a thick line of the stuff down his middle finger. Dean knew what came next.

“Please put your feet in the stirrups and scoot down to the end of the table.” Dean did as instructed.

“A little further, please.” Dean scooted down and the tip of his ass was hanging off the table. His legs were spread impossibly wide in the stirrups.

“I’m now going to examine your prostate.” And in went the finger. Dean couldn’t help it, he moaned and pushed back against it.

“Stay still!” Dean stopped.

Cas’ finger felt so damn good, and when he found Dean’s prostate and rubbed over it, Dean yelled. He couldn’t help it. He saw stars and colors behind his eyelids. 

A second finger went in and rubbed over his prostate until Dean’s cock squirted out a stream of pre cum.

Then the fingers were gone, and Dean had to resist whining. 

He lifted his head to see what Dr. Cas was doing. His eyes got big when he saw the metal apparatus in Cas’ hand.

“This is a speculum. I’m going to insert it. It will be cold but will warm soon.” Cas rubbed KY jelly all over it.

When it pressed to Dean’s hole, Dean gasped again. It felt weirder than hell. It slipped in and Cas pushed it a little ways. Dean tried not to wiggle but it was  _ cold _ ! True to the doctor’s word, it warmed up.

Then Cas began to twist a screw and it began to open. Dean clenched his fists in the pillow under his head. It felt like he was being opened to the absolute limit.

Cas sood back and smiled. “It will just take a moment to open you up for the next part of your exam, Mr. Winchester, Try to breathe through it.”

Dean took several deep breaths but it really didn’t help much.

Then he felt the metal being yanked out. He jumped a little,

“Stay still. And oh, by the way, don’t cum unless I tell you that you can.”

Dean heard the unmistakable sound of a zipper being lowered. He braced himself and moaned when he felt Cas’ thick cock breach his rim. Cas slid in fully and stopped. Dean wanted to tell him to move but he knew better.

Finally Cas wrapped his arms around Dean’s thighs and began to fuck him. Dean was really close to coming already but he knew he wasn’t allowed to.

Soon, it was like trying to hold back Niagara Falls with a teaspoon and a bucket.

“Fuck,. Sir..  doctor.. I’m too close…”

Cas pushed in as far as he could, then proceeded to use one hand to pinch Dean’s slit closed and use the other to squeeze Dean’s shaft at the bottom. Dean felt like his orgasm was shoved back into his balls.

“Please, Mr. Winchester, control yourself.”

Cas kept ramming in and out of Dean. Dean was reduced to a litany of, “Oh fuck! Fuck!”

Finally, after what seemed like days to Dean, he heard Cas’ voice.

“You can come now.”

Dean shot cum out of his cock like a geyser. He floated away, blissful and happy.

He was only partially aware when Cas came.

 

He came back to himself, clean and curled against Cas, warm in their bed.

“Welcome back, baby.”

Dean snuggled closer.

Cas ran his fingers through Dean’s hair and told him he was perfect, how much he was loved and what a good boy he was.

After drinking some juice and eating some fruit, Dean yawned.

“Can we do stripper and customer next?”

Cas  chuckled. “Of course we can.” That was the last Dean heard before he was asleep.

 


	3. Timestamp

**Summary for the Chapter:**

> Since so many of you wanted this... here is the stripper chapter!

Cas sat on the couch reading, when there was a knock on the door. He put the bookmark in place and went to answer it.

There stood a very handsome man is a business suit, smiling at him.

“Are you Cas Novak?”

Cas sighed. “Yes, I am. Who are you and what is this about?”

The guy smiled even bigger. “I’m your stripper!”   
Cas just stared at him for a moment, then, “I didn’t order any stripper, there must be some mistake.”

The guy pulled out a piece of paper and looked at it. “Cas Novak. 2114 E. Beehive Lane. That’s you, right?”

Cas nodded. “But I still didn’t…”

The guy cut him off. “It was paid for by your brother, Gabe. Hey, I’m paid for, might as well enjoy me, right?”

The guy pushed inside and looked around. He sat down a boom box and walked over to the coffee table. 

“Just gonna move this out of the way.”

Cas followed him, pinching the bridge of his nose. He sat down on the couch with an exaggerated sigh.

“Okay, let’s just get this over with.”

The guy frowned, “That’s no attitude to take. And call me Dean.”

He reached and pushed a button on the boom box and Marvin Gaye’s  _ Sexual Healing  _ began to play. Dean began to sway.

Cas had to admit, Dean was really sexy when he swayed his hips like that.

Dean pulled the jacket off his shoulders and let it fall slowly down his arms to the floor.

Cas stared.

Then Dean loosened his tie.

“Leave that on.” Cas’ voice was huskier than usual.

Dean grinned. He began to unbutton the crisp white shirt, one button at a time. His hips swayed with the music.

Then the shirt was falling down Dean’s arms just as slowly as the jacket did, until it fell to the floor.

Cas sucked in a breath at the vision of Dean’s chest. It had freckles and it was magnificent.

Dean started to really dance now. He shook his ass and thrust his hips forward very provocatively. Cas couldn’t even blink.

Then Dean unbuttoned the button on his trousers. He grabbed the zipper pull and very slowly, tooth by excruciating tooth, pulled it down.

Cas caught a glimpse of pink under Dean’s pants. 

Dean turned around and let his pants drop to the floor. As he stepped out of them Cas realized…  _ he was wearing pink panties _ .

Dean rotated his hips and then turned back around. His cock was clearly visible through the sheer pink satin. The head was just peeking out of the top.

Dean thrust his hips forward again and Cas licked his lips.

Dean danced to where Cas was sitting and turned around again, shaking his ass in Cas’ face. Cas made a grab for Dean’s ass, but Dean pulled away.

“No, no, no touching!”

Cas growled.   
The song was coming to an end. Dean twirled around and sat in Cas’ lap, his knees straddling Cas’ thighs. 

Cas pulled him into a filthy kiss and Dean let him. Their tongues played around each other for a few moments. 

Cas grabbed Dean’s ass and Dean laughed. “I take it you liked?”

“Fuck yeah, I liked.” Cas grabbed an ass cheek in each hand and ground up against Dean’s hardening cock. He grabbed Dean and threw him down on his back on the couch. Dean let out a tiny squeak which amused Cas a lot.

Cas ran his hand over Dean’s cock and Dean moaned as a drop of precum made its appearance at the tip. Cas leaned over and captured Dean’s mouth in a crushing kiss as he rubbed Dean’s cock. 

Dean gasped out, “That’s going to be extra…”

Cas laughed. He grabbed Dean’s panties and yanked them completely off. He reached between the cushions of the couch and came up with a bottle of lube.

Dean looked at it. “Uh, always prepared?”

Cas popped it open. “Like a boy scout.”

Cas poured some in his hand and said, “Lift ‘em.” Dean lifted his legs in the air, throwing one leg over the back of the couch and the other up near his head.

Cas pushed a lubed finger into Dean and Dean groaned.

Cas had Dean opened in no time. He grabbed his cock and pressed it to Dean’s slick hole. The head finally breached Dean’s sphincter and Dean gasped.

“Goddamn you’re big!”

Cas just smiled and slid in all the way.

Cas fucked Dean long and hard. Dean came all over himself but Cas just kept going. 

When he finally came, he shoved in as far as he could and came for what seemed like forever.  When it was done, he fell forward onto Dean.

They got their breath, Cas pulled back and went to get a cloth to clean Dean up.

While he was doing that, Dean smiled.

“How did you like this one, Sir?”

Cas smiled and leaned over for a kiss.

“You dance very well, Dean. Now, come on, it’s late, let’s go to bed.”

They slept with Dean as the little spoon and both had smiles on their faces.

  
  



End file.
